Novel strategy for the synthesis of chiral pseudo-ortho-substituted hydroxy[2.2]paracyclophane-based ligands from the resolved 4-bromo-12-hydroxy[2.2]paracyclophane as a parent compound

A simple and efficient resolution of racemic 4-bromo-12-hydroxy[2.2]paracyclophane into its enantiomers via diastereomeric esters with (1S)-(-)-camphanic acid was carried out. New synthetic routes to enantiomerically pure 4,12-dihydroxy- and 4-hydroxy[2.2]paracyclophanes starting from the enantiomers of an intermediate 4-bromo-12-hydroxy[2.2]paracyclophane are proposed. (C) 2008 Elsevier Ltd. All rights reserved.